title: Asymmetric synthesis of bicyclo[4.3.1]decadienes and bicyclo[3.3.2]decadienes via [6 + 3] trimethylenemethane cycloaddition with tropones.
abstract: The cyanosubstituted trimethylenemethane donor undergoes palladium-catalyzed [6 + 3] cycloaddition with a variety of tropones to yield bicyclo[4.3.1]decadienes in excellent regio-, diastereo-, and enantioselectivity. Products of the Pd-TMM [6 + 3] cycloaddition participate in a thermal [3,3] sigmatropic rearrangement to yield bicyclo[3.3.2]decadienes in good yield.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: McDougall
authors.forename: Olaf
authors.initials: O
authors.lastname: Hartmann
authors.forename: Peter T
authors.initials: PT
authors.lastname: Wathen
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D008055:Lipids / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D014334:Tropolone / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D001643:Bridged Bicyclo Compounds; D007659:Ketones; D008055:Lipids; D011090:Polyenes; C522820:trimethylenemethane; D010165:Palladium; D014334:Tropolone; C003730:tropone; D008697:Methane